Dear Rory
by ICanSeeYourFace
Summary: A series of letters, written to Rory by Jess. It's been approximately a year since Rory visited Jess in Philly, and now he feels there are some unfinished business between them. Follow his letters to Rory, as he tries to explain himself.
1. 10102007

**A/N**: Okey, my second fic. It's a series of letters, written by Jess to Rory. I know that the timeline is probably screwed up, but I needed it to be this way so it will work out in the end. Review please!

**Disclaimer**: I, the author of this story, do not own any of the characthers associated with Gilmore Girls. That honor belongs to the wonderful Amy Sherman-Palladino. I have no intention of making any money on this (in fact, I wouldn't be surprised if I'm losing money over it...).

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_Philadelphia, 10.10.2007_

_Dear Rory,_

_It's been almost a year (294 days to be exact, and no, I didn't use Yahoo to find that out), and I know I shouldn't be writing. You probably have a good life going, you've got Logan (for all I know, and it doesn't seem like much these days), and he's the one that makes you happy, right? However, I still have this need or whatever, to send you this. You know me, I don't come off as 'low-key' exactly, and I was always annoyingly persistent._

_Rory, we kissed. It wasn't me, it wasn't you, it was us. No matter what motives you had going on there, it was us. We kissed. I can admit that I made the move, but you responded. You've read my book, you know what made me write it. I think you know deep down inside I'll always have a thing for you, be it love or not (I tried talking to Matthew's poet, and he wasn't of much help, kept bringing Golda Meir into it…). You will always be my soft spot, and… I think I'm yours too. As far as I know, no one (not even Logan, and that says something) has hurt you as much as I have, and for that I will always kick my own ass. I left you, not only once, but… Well, let's just say I left you one time too many. I didn't handle things right, just like you said on the phone when I called you from Venice Beach. I just felt like I had disappointed you, made you turn away. I think I wanted to control the situation, be the one to leave, and then my dad turned up and left, and gave me the perfect excuse to skip town. Maybe I got the leaving part from him, who knows…_

_Anyway, I will always be a guy you remember, someone you think of in a different way. We are so alike, and still so different. I was not safe and loved by the town like Dean, I was not respected by your grandparents like Logan, and I'm not sure if I'm in Lorelai's good books yet. But you and me, we shared something, I don't know what really, it goes beyond the love for literature and the tendency to mercilessly mock movies we hate. Whatever dude came up with 'opposites attract' clearly must've had a vision of us two._

_I don't regret the kiss at Truncheon, I've almost made my peace with you going back to the guy that cheated on you. Overall, I have few regrets, but what I do regret is the stupid mistakes in my youth, the ones that cost me you, the only person I didn't want to lose. I screwed up, and here's where that got me: a published, reasonably successful writer, yes, but also a guy with a heart that can never love anyone but you. I'm sorry._

_I hope you're good._

Jess

_P.S I finished_ The Fountainhead_. I still don't know what she's rambling on about, and I still think she's a political nut. You owe me for bearing through Rand._

**A/N**: Okey, so good or bad? What do you think will happen next? ;)

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	2. 27102007

**A/N:** Second letter. I know many of you (if not all) expected a response from Rory, but nope... Those of you who are getting upset, don't be, by the end this will make perfect sense... At least I hope so. There may be a sequel to this story in the future. Thanks anyway for all the reviews on the first letter!

**Disclaimer:** I, the author of this story, do not own any of the characthers associated with Gilmore Girls. That honor belongs to the wonderful Amy Sherman-Palladino. I have no intention of making any money on this (in fact, I wouldn't be surprised if I'm losing money over it...).

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_Philadelphia, 27.10.2007_

_Dear Rory,_

_Take two. I tried writing you a letter two weeks or so ago, and I got as far as the post office when I decided not to send it, and I threw it away on my way home. It's funny how being a published writer, a pretty good one at that, doesn't guarantee you success in everything you write. When did I begin to suck at writing letters?_

_I bet Logan's having a breakdown if he's seen this, him and I never really got along. Although, I'd think he'd be smart enough to leave other peoples' letters alone. Wow, I almost considered Logan's feelings about this for a second. It must be some early Christmas-feeling._

_Anyway, I hope you're good. I take it you graduated Yale, so congrats to that, I bet you and Lorelai made faces at each other at the graduation ceremony, and that the town cooked up some nutty shindig for you. I would've sent you something, a book or a card, but I've been buried in work. Matt and Chris have been all over me for the past six months about writing a sequel, so I've been more or less locked up in my room to avoid their united efforts of ambushing me._

_I know you probably didn't expect me to write, last time we saw each other, it didn't exactly end well, or at least that's how I feel. I was disappointed Rory, and I think you know that. I asked you if everything was fixed, and you said yes. I've come to terms with you going back to Logan, even after what he did to you, I just wish it had never come to that. Every day, no exceptions, I regret everything I did that made me lose you. I was an ill-tempered smartass when we were together, and I should've been honest with you. But you have to understand, for a guy like me dating a girl like you, it made me think I was constantly disappointing you. I didn't want you to leave me, I don't think I could've taken that, so I took matters in my own hands. Not my smartest move, but what's done is done, I guess._

_I tried having relationships while I was gone, I don't deny it, but it always came down to the same thing. They weren't you. You're my soft spot Rory, I can never get over the fact I lost the person that meant the most to me. I'll always have a thing for you, I'm not sure you could call it love, but in lieu of a better expression… I'll always love you. Don't look like that now, and don't worry. You won't catch me barging through the door, and pull a stunt like the one at that fire-something-or-other festival. I know better than that._

_You know, I made it through_ The Fountainhead_. I'm not impressed, and in my eyes Ayn Rand is still a politcal nut. I think this calls for you reading some Hemingway to even the score._

Jess

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**A/N:** Okey, so it's pretty repetitive from letter one, but he's just trying to get it right, and well... the guy's frustrated. :D


	3. 14112007

**A/N:** Okey, so I'm putting up chapters 3 and 4 at the same time, otherwise I suspect you'd be too bored, and I want to get on with the story. I promise there's a point with all these discarded letters, or at least in my mind there is… As always, thank you so much for the reviews, and bear with me (and Jess…) for a while longer!

**Disclaimer:** I, the author of this story, do not own any of the characthers associated with Gilmore Girls. That honor belongs to the wonderful Amy Sherman-Palladino. I have no intention of making any money on this (in fact, I wouldn't be surprised if I'm losing money over it...).

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_Philadelphia, 14.11.2007_

_Rory,_

_Third time's the charm, and I can't believe I just wrote that. Well, there it is, and here I am, on my third attempt to write you a letter, expressing my… God, I don't even know why I'm writing. Seriously, this sucks. I managed to write a book, a book that has sold pretty well the past year, but I can't write a freaking letter! I think I know now why I didn't hear from you that summer when you were in Washington._

_I browsed around Yale's homepage, I saw you graduated, congrats to that. Bet you and your mom pulled some kind of stunt at your graduation, and that you and that whole nutty town celebrated in some strange way. I would've sent you something, but I've been held up by Matt and Chris, plus I didn't know how you'd take getting a present from the guy you kissed in Philly just to try and get back at your boyfriend. No, I'm not bitter. I've actually sort of accepted the situation. I have no pull with you, I never imagined I had. I just care for you Rory, always have, always will. Sounds so cheesy, and totally not me, but then again, saying 'I love you' and immediately skip town afterwards isn't any better. It seems all I've ever done is make an ass out of myself._

_You know, you're so hard to make up for. Luke was easy, he saw I had grown up, gotten a grip and so on. He finally cashed the money I owed him. He was content with seeing me straightened out, and I was happy to see him that way. You're different Rory. I did stuff to you I never expect to be forgiven for. I can never make up for skipping out of your life at the most inconvenient times, and then pop back in just when you started getting over me. Perhaps I deserved the kiss-debacle at Truncheon. I let you down and left you so many times, perhaps it wasn't more than fair that I got to experience what I made you experience too many times._

_I hope you're good. I want you to be good. I've got a piece of news for you. I got through_ The Fountainhead_. I'm not impressed and in my opinion it calls for you reading Hemingway._

_I'm… oh, screw that…_

Jess


	4. 25112007

**A/N: **So, chapter 4. Yes, it's repeptitive, and he keeps on rambling about the same stuff all the time, but he's trying to get it right, and you know how it is when you're trying to get something right… One chapter left, and I'll promise all these discarded letters will make sense… At least I hope so.

**Disclaimer:** I, the author of this story, do not own any of the characthers associated with Gilmore Girls. That honor belongs to the wonderful Amy Sherman-Palladino. I have no intention of making any money on this (in fact, I wouldn't be surprised if I'm losing money over it...).

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_Philadelphia, 25.11.2007_

_Rory,_

_This is getting very annoying, I've been trying for over a month to write you a stupid letter, and the damned thing has never even made it to a mailbox. This if my fourth, and I'm not exactly hopeful that this one will turn out any different than the others._

_Easy things first. I made it through_ The Fountainhead_. Ayn Rand is still a nut, and I will never ever read that damned thing again, and you owe me. I'm sending you a Hemingway for your birthday, and you will happily read it._

_This is the part where I want to have my head examined, I have no idea where all my bright plans for this letter goes, but I'd sure like to know. It seems every time I sit down to write you I get a black out, and I scribble down something that never make any sense once I get as far as going out to mail it._

_Bottomline is, I was disappointed like hell when you walked out of Truncheon. I've been trying to tell myself otherwise through three letters, but I'm not fine. We kissed Rory, a kiss like the ones we used to exchange back in the days. You told me you had fixed everything, including the Logan-situation, and you led me on. God, had I only refrained from being such an ass when we were together I wouldn't be having this problem. I can't get you out of my head Rory._

_I'm sorry for everything I did. For leaving, returning, and breaking your wrist and your heart. I'm sorry for not being honest, for hurting you and just about every other person that even remotely liked me._

_I'm sorry._

Jess


	5. 15122007

**A/N:** Okey, so we're finally here, chapter 5! Your wait is over, and we'll finally get to see if Jess got his act together and sent Rory a letter. Yey!

**Disclaimer:** I, the author of this story, do not own any of the characters associated with Gilmore Girls. That honor belongs to the wonderful Amy Sherman-Palladino. I have no intention of making any money on this (in fact, I wouldn't be surprised if I'm losing money over it...).

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"Mom?" Rory called out when she entered through the door.

"Loinfruit! Kiddo!" Lorelai exclaimed, hearing her daughter in the hall. "What took you so long, why didn't you answer mommy's phone calls?"

"I was driving, don't you know what they say about cell phones and driving?"

"That they are an excellent way of saving time if combined?" Lorelai suggested, loading the coffeemaker.

"That, and that it is illegal." Rory answered with a smile.

"Oh, right. Anyway, mrs. Stalin just called, pestering me again. You are gonna be home for Christmas, right? No surprise-snatchings?"

"I will be home," Rory answered, entering the kitchen. "We finished in Washington yesterday, so I'm homefree until after New Year. Three lovely weeks of movies, junkfood, Luke's coffee and dinner with grandma and grandpa"

"I'll just ignore the last part. Oh, by the way, you've gotten a Christmas card."

"I have?" Rory asked, surprised. "But they always come addressed to both of us."

"This one's for you." Lorelai said, fingering the card.

"What does it say? Who is it from?"

"It's… It's from Jess."

Rory stopped silent.

"Can I have it, please?"

Lorelai handed Rory the card, and Rory took it, and went into her room, closing the door. She sat down on her bed, her faithful bed that had been with her through all her years. She looked at the card, a pretty standard one, with Santa and his reindeers. Slowly she turned the card, expecting to see the back of the card covered with Jess' familiar handwriting. To her surprise, the card had four short lines:

_Merry Christmas and a Happy New Year.  
__My four previous attempts to write you a letter boiled down to this.  
__I'm sorry, for this and everything else. _

_Jess._

She read the card over and over again. He was sorry.

"So am I…" she whispered to the cold darkness outside her window, putting away the card. She took out a notebook out of one of her bags, along with a pen, intending on writing a letter to Jess. She knew he had wanted to say more, and she wanted to know what.

Ten minutes later she still hadn't gotten any further than _"Dear Jess,"_. It was Washington all over again! Her mom was already suspecting something was wrong, as Rory had declined Lorelai's coffee-offer five minutes or so ago. Suddenly, she knew what she had to do, it was the only way. In the middle of the night she wrote a note to Lorelai _("Mom, had to go away. Will be home for Friday night dinner. /Rory"_), took her handbag and the card, snuck out, got into her car and drove away into the night. Destination?

Philadelphia.

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**A/N:** Okey, so this one will definitely have a sequel, and I'm already working on it. Please review, and if you have any suggestions or wishes for moments or such that you'd like to see in the sequel, please post it in the review or PM me. Thanks!


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